Anon asks: Isaac! I’m obsessed with stalking my boyfriend’s ex girl. They broke up after two years and she was devastated for months; she even called him in the middle of the night once! I know they were open-ended and kept talking until we began dating, even though he downplays the recency/seriousness of the relationship. I don’t think he has lingering feelings for her but I can’t help feeling threatened/fearful that they’ll get back in contact. It’s been a year of stressing — how can I put this to bed?

Anon asks: Hey Isaac, I was hoping for some insight. I like this girl but the problem is that I’m afraid of asking her out because she comes from a much wealthier background and I’m scared of embarrassing myself. Any advice or experience with this sort of thing?

Anon asks: Hey Isaac, I’ve liked this girl for a while now but I’ve never explicitly told her, and now she’s interested in my friend. I really want to tell her but I risk upsetting the other man in question. Any advice?

Hey, gidday mate! I was in a similar friend zone situation when I was a teenager. I was semi-obsessed with this friend of mine, and I never 100% told her, and then she fell for one of our friends and they started dating and it sucked.

Anon asks: My boyfriend and I have struggled with communication since day one. Five months ago he broke up with me for being “too flirty” and because “our personalities are too different”. I spent two months working on myself and eventually we got back together. In the first month he showed he hadn’t changed at all, I called him on it, and things have been amazing ever since. However, two days ago in a drunken argument he broke up with me. The break up didnt last longer than a night’s sleep, but how can I still trust him?

Hey, gidday mate. Let’s call a spade a spade: Maybe you can’t trust him. Maybe you guys aren’t right for each other.

Anon asks: Hi Isaac. My long distance relationship ended because he wasn’t willing to commit. We still FaceTime semi-regularly and have a great connection but I want more then he’s offering me. I want him to stay in my life but I don’t know if it’s healthy to settle for breadcrumbs? And if I did decide to stop talking to him a portion of my intention would be because I was wanting him to chase after me and I don’t know if that’s healthy either…

Hey, giddy mate! There’s this philosophy that I try to adhere to that states that it’s easier to act your way into right thinking than it is to think your way into right action. What it means is that if you just go ahead and do the right thing (and continue to do the right thing), at some point your brain/heart will follow suit.

Anon asks: One of my best guy friends recently got out of an eight year relationship. A couple months after they broke up we ended up hooking up, and then a month after that we hooked up again, but it’s super confusing — he’ll say one thing then act a different way and when I try and have a conversation about the situation for some clarity he won’t respond. Now we haven’t talked in two months despite being best friends. I have very strong feelings for him, thoughts? Help!

Anon asks: Hey Isaac, I’m 29 and moved to New York City from London four years ago and I love it, EXCEPT: Pretty much every dating experience I’ve had here has been casual or bad. It seems hard to meet guys here who are ready for more, and it feels like such a tough place to find love. I’ve started really feeling anxious about my future here. Do you think it’s crazy to consider moving somewhere that seems to have more of a healthy balance?

Hey, gidday mate! I moved to New York five years ago, and it hasn’t been my experience that people here are only looking for casual relationships. I mean, you’re not, and a lot of my friends are in relationships (and I’m in one), so there are obviously people out there who want something serious.

Anon asks: Hi Isaac. I started seeing a good friend after confessing we’d both adored each other for years. He said he wanted to be with me; before long though, he was living up to his reputation and treating me like just another random girl. He freaked, ghosted and broke my heart after five months. We cut contact, then a month later he showed up at a party with a new girlfriend and they put on such a show — I feel sick and our friends are shocked! Why would he commit to this girl but not to me?

Hey, gidday mate. It sucks, but you said it yourself: He lived up to his reputation.

Anon asks: Last night my boyfriend of two years said it’s over. We’re both mid-late 20s and I thought he was the one, but he came clean and said he’d become less invested in the relationship than me. We both love each other dearly and spent last night crying and laughing about all the good times. More than anything we both want to be friends in the future — any tips on how to get through and remain pals?

Hey, gidday mate. I’ve been through a few of those, “But I thought this one was the one,” situations and the end is never easy. So first things first I’m sorry for what you’re dealing with. Now, let’s talk how to stay friends with an ex.

Anon asks: Hi Isaac! I’ve been seeing this guy for about six months and he is fantastic. He’s loving, kind and treats me with respect. I’m still very hurt/angry from my last relationship even though it ended 18 months ago. My ex — who I was with for five years — was manipulative and used me then broke up with me to ‘be alone’ to deal with his depression, but just turned to drugs and got a new girlfriend. Any advice on how to move on?

Hey, gidday mate! I’m a huge believer in staying single while we’re working through the pain of a breakup. When we’re not over our exes, we’ll often carry the baggage of our past relationship into our new relationship, and it can cause massive problems for everybody concerned.